Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 19, Pages 6336-6342Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja070259i
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Funding
- NCI NIH HHS [CA70375, R01 CA070375, R01 CA070375-11] Funding Source: Medline
- NIGMS NIH HHS [F32 GM072296, GM49631, GM72296] Funding Source: Medline
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Concise asymmetric total syntheses of the fungal metabolites (-)-stephacidin A, (+)-stephacidin B, and (+)-notoamide B are described. Key features of these total syntheses include (1) a facile synthesis of (R)-allyl proline methyl ester, (2) a revised route toward the pyranoindole ring system, (3) a novel cross-metathesis strategy for the introduction of important functional groups, and (4) an S(N)2' cyclization to form the [2.2.2] bridged bicyclic ring system. Furthermore, our synthesis has taken advantage of microwave heating to shorten reaction times as well as increase yields for the preparation of vital intermediates.
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